Azodyestuffs



Patented Oct. 2, 1934- nairss srArss PATENT FFEQ AZODYESTUFFS William Edward Kemmerich, Nyack, N. Y.

No Drawing. Application October 17,1931;

Serial N0. 569,537 t 6 Claims. (CL 260-95) 3-hydroxy-naphthoic acid combined with a di-' azocompound, having the-following constitution:

of pigment colors of excellent fastness', and give when produced on the fibre from a yellowish orange to red to blue and black shades of great intensity and excellent fastness to light, soaping and chlorine. The 2 3 hydroxy-naphthoyl 2 aminodiphenylides and substituted 2-3-.hydroxy naphthoy1-2'-aminodiphenylides have when dissolved in an alkali a great affinity to the cotton 40 fibre, so that the developed dyestuif shows a very good fastness to rubbing. It is therefore obvious that these new dyestufis represent-a very valuable addition in thisclass of azo dyestuffs. l

The 2-3 hydroxynaphthoyl-Z'-aminodipheny1- ides may be prepared according to the process described in U. S. Patent 1,101,1l1 by allowing a 2'-aminodiphenyl or a substituted 2'-aminodiphenyl to react on 2 -3-hyd roxynaphthoic acid in the presence of a dehydrating agent, or by forming first the chloride of 2-3 -hydroxynaphthoic acid. and bringing this product in contact with a 2-aminodiphenyl or a substituted 2 aminodiphenyl. w v

The so obtained 2-aminodiphenylide of-2-3- hydroxynaphthoic acid for instance crystallizes The dyestuffs can be used for the production from toluene in the form of small sand colored crystals having a melting point of about 170 I centigrade,

To further illustrate my invention the following examples are given, the parts being by weight, but it is understood that my invention is not limited to the particular products mentioned'or to the reaction conditions given therein.

Example 1 A diazo solution prepared in the usual manner from 138 parts of ortho-nitraniline is run under continuous stirring into 3&0 parts of 2-3-hydroxynaphthoyl-2-aminodiphenyl dissolved in diluted caustic soda solution containing sufficient sodium acetate to counteract the excess mineral acid of the diazo solution. A bright yellowish orange is formed as a flaky precipitate, which soon settles. It is filtered andwashed. The pigment dyestufi so obtained may be used as such or it may be transformed into its metal lakes, such as the chromium-, t'ungsten-, aluminumor other lakes. The product corresponds probably to the following formula:

The same color may also be produced on the fibre in the following way:

Example 2 Cotton material well w-etted out is impregnated with 5 grams of 2-3-hydroxynaphthoyl-2-amino diphenyl dissolved in'15 cc. of 33% caustic soda solution, 20 cc. of Turkey red oil, 5 cc.ethy1 alcohol and made up to 1000 cc. with hot water. 'The material is treated with this solution for about 30 minutes, then wrung out well and developed in the following diazo solution.

3.75 grams of ortho-nitro-aniline are diazotized in the usual: manner and the free mineral acid neutralized with sufficient sodium acetate; this solution is then diluted with cold water to the desired volume after 25 g. of sodium chloride have been added.

A very yellowish bright orange is so obtained on the fibre of excellent general fastness properties. Hot soaping after rinsing increases the brilliancy of the shade.

Example 3 The impregnation of the cotton material is carried out as in Example 2 except that instead of 5 g. 2-3-hydroXynaphthoyl-2'-aminodiphenyl, 6 g. of 2-3-hydroxynaphthoyl-2-amino-dichlorodiphenyl are used.

' The developing solution is prepared as follows:

5 g. meta-nitro-ortho-anisidine are diazotized in the usual manner and the diazo Solution is neutralized with sodium acetate andv r" t -OH I OONHV The 2 3 -hydroxynaphthoyl- 2 -aminodiphenyls and their substituted products may also be used for textile printing. This can be done by first padding the material with a solution of these products in caustic soda and then'printing the developing diazo solution on'the dried material with the aid of a printing paste It is further possible to combine the 2-3-hydroXynaphthoyl-2-aminodiphenyl with the nitrosamine salts of diazotizable aminobodies in an alkaline solution and a printing paste and to develop the colors with the aid of an acid after drying.

The following table gives the color of a number of dyestuffs according to my invention:

It has been found that the dyestuffs derived from the 2-3-hydroxynaphthoyl-2'-aminodiphenyl and from substituted 2-3-hydroxynaphthoyl- 2-aminodiphenyls can also be advantageously produced on silk, viscose, cuprammonium silk and cellulose acetate silk.

Now what I claim and desire to secure by Letters Patent is the following:

1. As compounds, azo dyestuffs corresponding to the general formula:

NzN-aryl CONH- where aryl means a radicle of a diazotized aromatic amine, having hydrogen, halogen nitro-, hydroxy, methoxy-, ethoXy-, methyl-, ethyl,

phenyl-groups in one or more positions, which +x CONE- where X may be'hydrogen, halogen, or one or more of the following groups: omocm, OCzHs, CH3, CzI-Is, CsHsfNOz.

5. Process for manufacturing new azo dyestuifs which process comprises combining any aromatic diazo compound with 2-3-hydroxy-naphthoyl-2'- 13s.] aminodiphenyl, having a substituted diphenyl groupas enumerated in claim 4.

6. Fiber dyed with the dyestuffs as claimed in claim 4.

WILLIAM EDWARD KEMMERICH.

Diazo compound of- Combined with Shade Ortho-nitraniline 2-5-dichloraniline 5-nitr0-1-2-tolnirli1m Z-aminodiphenyl Para-nitraniline 3-amino-4-cresol methylethen Dimethyl-para-phenylene-diamine l-amino-2-111ethoxybenzene-azo-l-naphthylamine Safiranine l-naphthylamine. Ortho-ehloreniline.-

Ortho-dianisidine 4-amino-diphenyl. l l

2-3-hydroxynaphthoyl-2-aminodiphenyl Bright-blue.

d Bordeaux. Orange.

Yellowish orange. Orange. Yellowish red. Bright red. Bluish red. Bluish Bordeaux. Violet. Blue-black.

Blue. Red. 

